Phthalimide derivatives and their use as plant growth regulants

ABSTRACT

The invention is a novel class of phthalimido derivatives represented by a formula: ##SPC1## 
     Or ##SPC2## 
     Wherein W is hydrogen or alkyl C 1  -C 4  ; X and X&#39; each represent hydrogen, halogen, alkyl C 1  -C 4 , CF 3 , alkoxy(C 1  -C 4 ), benzyloxy, di(C 1  -C 4 )alkylamino, C 1  -C 4  alkylthio, hydroxy, C 1  -C 4  alkylsulfonyl, alkanoylamino C 1  -C 4  or nitro; Y is --COOR 3 , --CONHR 8 , --CONR 3  R 4 , --CONHN(R 5 ) 2 , --CONHN + (R 6 ) 3  . halide - , --CN or --COR 7  with the proviso that at least one of X and X&#39; is a substituent other than hydrogen; R 1  and R 2  each represent alkyl C 1  -C 4  or when taken together with the carbon to which they are attached form cycloalkyl C 4  -C 11  optionally substituted with methyl; R 3  and R 4  each represent hydrogen or alkyl C 1  -C 4  ; R 5  and R 6  each represent alkyl C 1  -C 2  ; R 7  is halogen and R 8  is --CH 3  or ##SPC3## 
     Where Z and Z&#39; are hydrogen, alkyl C 1  -C 2 , halogen, --CF 3  or --OCH 3 ,     is a single or double bond with the proviso that there be only 0 or 1 double bond in the ring and a method for regulating the growth of plants with these compounds and with compounds having the above structure wherein X and X&#39; each represent hydrogen.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of our co-pending applicationSer. No. 348,355 filed Apr. 5, 1973, which is a continuation-in-part ofco-pending Ser. No. 282,537 filed Aug. 21, 1972, both now abandoned.

BACKGROUND OF THE INVENTION

1. Field of the Invention:

The invention pertains to the chemical arts, i.e., phthalimidederivatives and their use as plant growth regulants.

2. Description of the Prior Art:

Upham's U.S. Pat. No. 2,999,863 (1961) disclosesalpha-phthalimidoacetamide derivatives as anticonvulsants and a methodfor their manufacture.

SUMMARY OF THE INVENTION

The invention is novel compounds represented by a formula: ##SPC4##

Or ##SPC5##

Wherein W is hydrogen or alkyl C₁ -C₄ ; X and X' each representhydrogen, halogen, alkyl C₁ -C₄, CF₃, alkoxy (C₁ -C₄), benzyloxy, di(C₁-C₄)alkylamino, C₁ -C₄ alkylthio, hydroxy, C₁ -C₄ alkylsulfonyl,alkanoylamino C₁ -C₄ or nitro; Y is --COOR₃, --CONHR₈, --CONR₃ R₄,--CONHN(R₅)₂, --CONHN⁺(R₆)₃ halide⁻, --CN or --COR₇ with the provisothat at least one of X and X' is a substituent other than hydrogen; R₁and R₂ each represent alkyl C₁ -C₄ or when taken together with thecarbon to which they are attached form cycloalkyl C₄ -C₁₁ optionallysubstituted with methyl R₃ and R₄ each represent hydrogen or alkyl C₁-C₄ ; R₅ and R₆ each represent alkyl C₁ -C₂ ; R₇ is halogen and R₈ is--CH₃ or ##SPC6##

where Z and Z' are hydrogen, halogen, alkyl C₁ -C₂, --CF₃ or --OCH₃, isa single or double bond with the proviso that there be only 0 or 1double bond in the ring; mixtures of said compounds are also within thescope of our invention. Isomeric mixtures of the above-identifiedcompounds are also contemplated and are of particular interest in thisinvention. These compounds, as well as compounds of the above structurewhere X and X' are both hydrogen, are useful as plant growth regulatingagents, as intermediates for the preparation of plant growth regulatingagents, or as both plant growth regulants and intermediates therefore.Compounds of the above structure where Y is --COR₇ and X, R₁, R₂ and R₇are as described, are primarily useful as intermediates for thepreparation of the plant growth regulating agents. Similarly, compoundshaving the above formula where Y is --COOR₃ and R₃ is hydrogen, are alsouseful as intermediates; however, many of these compounds are alsohighly effective plant growth regulants.

DETAILED DESCRIPTION

In accordance with the invention, the above-identified phthalimidoderivatives can be prepared by reacting the appropriateα-aminocarboxylic acid or acid derivative with a phthalic anhydride,preferably in the presence of an aprotic solvent and a tertiary amine,such as triethylamine. Among the solvents which are useful in carryingout this reaction are: toluene, xylene, dimethylformamide and aceticacid. In practice, it will be found that the reaction can be conductedat a temperature between about 100°C. and 175°C., and preferably between100°C. and 150°C. Alternatively, the required product can be prepared byfusing the α-amino acid or acid derivative and phthalic anhydride attemperatures between about 150°C. and 250°C., but preferably at 180°C.to 210°C. The reaction can be graphically illustrated as follows:##SPC7##

where X, X', R₁, R₂ and Y are as indicated above, with the exceptionthat Y cannot be --COR₇ or --CONHN⁺(R₆)₃. halide⁻. This reaction mayalso be employed for the preparation of the 1,2,3,6- or3,4,5,6-tetrahydrophthalimido or 1,2,3,4,5,6-hexahydrophthalimidoderivatives. Reaction conditions are the same as described aboveexcepting that the appropriate tetrahydrophthalic or hexahydrophthalicanhydride is substituted for phthalic anhydride.

While this high temperature reaction described above is effective forthe preparation of all of the above-identified compounds, we havediscovered that when Y is --CN and the reaction is carried out at atemperature of about 60°C. or less, a phthalamic acid is formed whichcorresponds to the α,α-disubstituted-α-aminonitrile used. The phthalamicacid can then be cyclized to the corresponding phthalimidonitrile. Thisreaction is described in greater detail below. In the case where Y is--COOH, the thus-formed acid can then be converted to the correspondingacid halide by heating the acid with thionyl chloride, thionyl bromide,phosphorus pentachloride, or the like, preferably in the presence of anaprotic solvent, aromatic or chlorinated hydrocarbons, such as benzene,xylene, toluene, methylene chloride, chloroform or dichloroethane. Thereaction is graphically illustrated below, wherein thionyl halide, i.e.chloride or bromide, is representative of the halogenating agentemployed. ##SPC8##

wherein X, X', R₁, R₂ and R₇ are as described above. Conversion of the(tetrahydrophthalimido)acetic acids and the (hexahydrophthalimido)aceticacids to their corresponding acid halides may also be achieved by theabove reaction using the appropriate acid as starting material.

The thus-formed acid chloride or acid bromide can then be converted tothe corresponding amide by reaction thereof with ammonia, dialkylamineor dialkyl hydrazine, at a temperature between about -20°C. and +25°C.,and preferably -10°C. to +15°C. This reaction is preferably carried outby dissolving the acid halide in a solvent, such as acetone or awater-miscible ether, such as tetrahydrofuran, dioxane, or the like, andadding this solution to an aqueous solution of the amine. Alternatively,the amine can be added directly to a solution of the acid halide in theabove solvents or in an aprotic solvent, such as toluene or chloroform.The reaction can be graphically shown as follows: ##SPC9##

wherein X, X', R₁, R₂, R₃, R₄, R₅ and R₇ are as defined above.

Similarly, these reactions can be employed to prepare the(tetrahydrophthalimido)acetamides and the(hexahydrophthalimido)acetamides using the appropriate acid chloride asstarting material.

Alternatively, the phthalimido acetamides in which R₄ is hydrogen may beprepared by reacting the appropriate phthalic, tetrahydro- orhexahydrophthalic anhydride with the appropriatelyα,α-disubstituted-α-aminonitrile to give the corresponding phthalamicacid. This reaction is carried out at temperatures from about 20°C. to60°C. in an inert solvent such as ether, tetrahydrofuran, chloroform,methylene chloride, benzene, toluene, and the like. The thus-formedphthalamic acid is then cyclized to the corresponding phthalimido,tetra- or hexahydrophthalimidonitrile by heating with a dehydratingagent such as acetic anhydride, acetyl chloride, thionyl chloride or thelike at temperatures from about 0°C. to 100°C. Hydration of thethus-formed phthalimidonitrile is preferably carried out with a strongacid such as sulfuric acid, preferably in the presence of a non-misciblesolvent such as methylene chloride or chloroform and the like attemperatures from about -10°C. to +30°C. These reactions are graphicallyillustrated by using the substituted phthalic anhydride as an example asfollows: ##SPC10##

wherein X, X', R₁ and R₂ are as defined above. Where a hydraziniumhalide is desired, an amide having the formula: ##SPC11##

where W, X, X', R₁, R₂, R₅ and are as defined above, can be treated withan alkyl halide in the presence of a solvent, such as tetrahydrofuran,ether, dioxane, benzene, chloroform, or the like, at an elevatedtemperature to yield the desired corresponding hydrazinium halide. Thehydrazinium salts in the tetrahydro- and hexahydrophthalimido series areprepared in the same manner.

To obtain the active phthalimido ester having the formula: ##SPC12##

where W, X, X',R₁, R₂ and are as defined above, and R₃ is alkyl C₁ -C₄,the corresponding acid, i.e. where R₃ is hydrogen, is treated with adiazoalkane C₁ -C₄ in the presence of a solvent, such as an ether. Thisreaction can be carried out at a temperature between -10°C. and +30°C.

Alternatively, the appropriate α-amino ester can be allowed to reactwith the appropriate phthalic tetrahydrophthalic or hexahydrophthalicanhydride to afford the phthalamido, tetrahydrophthalimido orhexahydrophthalimido ester, or the acid halide, prepared as above, maybe treated with a lower C₁ -C₄ alkanol in the presence of an acidacceptor, such as pyridine, triethylamine, sodium bicarbonate, and thelike.

The phthalimido nitrile can be obtained by dehydration of thecorresponding amide using titanium tetrachloride, phosphorus pentoxide,phosphorus oxychloride, acetic anhydride, trifluoroacetic anhydride, orthe like, in the presence of a solvent, such as benzene,tetrahydrofuran, or the like. This reaction can be carried out at atemperature between about 0°C. and 100°C.

Alternatively, these compounds can be prepared by reacting a compound ofthe formula: ##EQU1## where R₁, R₂ and Y are as indicated above, withthe exception that Y cannot be --COR₇ or --CONHN⁺(R₆)₃ . halide⁻, with asubstituted phthaloyl chloride of the formula: ##SPC13##

where W, X and X' are as indicated above.

Alternatively, these compounds can be prepared by reacting the compound:##SPC14##

where W, X and X' are as defined above and R₉ is alkyl C₁ -C₄ with acompound of the formula: ##EQU2## where R₁, R₂ and Y are as indicatedabove, except that Y cannot be --COR₇ or --CONHN⁺(R₆)₃ . halide⁻, togive a product: ##SPC15##

or ##SPC16##

which can then be cyclized to give the product: ##SPC17##

or ##SPC18##

where W, X, X', R₁, R₂ and Y are as indicated above, except that Ycannot be --COR₇ or --CONHN⁺(R₆)₃ . halide⁻.

The plant growth regulating effects obtained with compounds having thestructure: ##SPC19##

or ##SPC20##

where W is hydrogen or lower alkyl C₁ -C₄ ; X and X' are hydrogen, alkylC₁ -C₄, halogen, alkanoylamino C₁ -C₄, CF₃, alkoxy C₁ -C₄, benzyloxy,di(C₁ -C₄)alkylamino, C₁ -C₄ alkylthio, hydroxy, C₁ -C₄ alkylsulfonyl,or nitro; Y is --COOR₃, --CONHR₈, --CONR₃ R₄, --CONHN(R₅)₂,--CONHN⁺(R₆)₃ . halide⁻ or --CN; R₁ and R₂ each represent alkyl C₁ -C₄,or when taken together form cycloalkyl C₄ -C₁₁ optionally substitutedwith methyl; R₃ and R₄ each represent hydrogen or alkyl C₁ -C₄ ; and R₅and R₆ each represent alkyl C₁ -C₂ ; and R₈ is --CH₃ or ##SPC21##

where Z and Z' are hydrogen, halogen, alkyl C₁ -C₂, CF₃ or --OCH₃, arewidely varied and most remarkable.

One very surprising aspect of this invention is the finding thatvirtually every plant species tested in accordance with the inventionresponded, rather dramatically, in a very desirable manner regardless ofthe method of application employed or the specific compound orformulation used.

Another very surprising aspect of the invention is the finding thatalthough the plant growth regulating effects of the compounds within thegeneric class described above sometimes varies from plant to plant andspecific compound to specific compound, all compounds are highly activeat low rates of application and none appear to be phytotoxic even whenapplied at rates as high as 32 pounds per acre in the treated area. Inpractice, it will, therefore, generally be found desirable to employfrom about 0.06 pound to 32 pounds per acre, and preferably 0.06 poundto 4.0 pounds per acre of the active phthalimido compound in the treatedarea to obtain the desired plant growth regulant effect.

Among the desired effects obtained with the compounds of the inventionare:

A. increased internode growth evidenced by longer internodes havingincreased dry weight;

B. increased leaf size evidenced by increased dry weight;

C. induced flowering and/or bolting in certain varieties of plants;

D. increased set in tuberous plants;

E. increased rate of seedling emergence and increased height of seedlingplants; and

F. delay of senescence, especially in flowering plants;

G. causes fruit clusters, e.g. grapes, to open or spread reducing thelikelihood of fungal attack.

The advantages obtained with increased internode length are multiple.They include, in addition to a general increase in the total size andweight of the plant, opening or spreading of plant leaves whichgenerally makes the plant less vulnerable to disease through betterventilation. Moreover, increased internode length has particularadvantage for crops, such as soybeans, cotton, tobacco, sugar cane,timber and seed corn. With soybeans it has been found that the lowerpods, normally lost at harvest because they are below the level of theharvesting elements, are now sufficiently elevated by the elongation ofthe plant internodes to be harvested. This mechanism thus increasessoybean yields a significant 3 to 4 bushels per acre and facilitatesmore rapid harvest. Similarly, elongation of cotton and tobaccointernodes elevates the lower cotton bolls and lower tobacoo leavessufficiently to prevent their normal destruction or damage by theelements (i.e. abrasion, disease, etc.).

With sugar cane and timber, longer internodes produce larger cane andtrees resulting in greater yields of sugar and lumber, whereas, longerinternodes in seed corn raises the corn tassel, i.e. the male organ ofthe plant, high enough that it can be removed from all plants in a fieldwith a single cutting before pollination occurs. Controlled pollination,to provide a desired hybrid corn, can then be effected at will.

The advantage of increasing the leaf size of plants is obvious and ofparticular importance for those plants wherein the leaves constitute themarketable crop. Tobacco, forage crops and leafy vegetables, such asspinach, swiss chard, lettuce and cabbage, exemplify such crops.

Accelerated flowering and bolting is important for crops which are grownfor seed. Among the important crops of this type are lettuce, radish,sugar beets, red beets, brussel sprouts, broccoli and carrots.

Increased set in tuberous plants, such as potatoes, is another importantadvantage of this invention, since the treated plants develop two tothree times as many potatoes as the untreated plants. Moreover, thepotatoes on treated plants are vastly more uniform than those onuntreated plants, although they are only average in size. This, however,is an advantage where the potatoes are to be used for canning.

Enhancement of the rate of seedling emergence and increased height ofseedling plants are still other advantages obtained with the compoundsof this invention. In certain regions, for example, the MississippiDelta in the United States, soil structure and moisture content canpresent serious problems for the farmer. In order to assure germinationof plants in this region, it is sometimes necessary to plant ratherdeeply. If the plants emerge before a heavy rain, they usually maturenormally. However, when heavy rains occur between planting andemergence, it is not an uncommon occurence to find that a crusting ofthe soil surface takes place. Seeds which have not emerged by this timecannot break the crust and generally rot in the ground. Thus, the onlyrecourse to the farmer is to replant.

It would, therefore, be most advantageous if a compound could be foundwhich would hasten germination and enhance the growth rate of seedlingplants.

A still further advantageous effect obtained with the compounds of thepresent invention is the delay of senescence in plants. This effect isespecially important to nursery men and florists who desire to extendthe life of the blooms in flowering plants.

Surprisingly, we have discovered that the phthalimido compoundsdescribed above, particularly the halo-substitutedphthalimidocycloalkylcarboxamides, provide these advantages.

We have also found that the effectiveness of the compounds of theinvention as plant growth regulating agents is not limited byformulation or method of application. The active compounds may beformulated as dusts, dust concentrates, wettable powders, emulsifiableconcentrates, soil drenches, granular formulations, and the like. Theymay be applied in combination with a solid or liquid diluent by avariety of methods, including: root dips, seed coatings, transplantwater, foliar application, preplant incorporation in the soil,preemergence soil application, and low volume application in the form ofdiscrete droplets having a mass median diameter of from 25 to 150microns.

Typical formulations which are useful in the practice of the presentinvention include: wettable powders, dusts dust concentrates, granularformulations and flowable formulations.

Wettable powders can be prepared by blending the active phthalimidederivative with a solid carrier, such as attapulgite, kaolin,diatomaceous earth, silica, or the like, and a small amount of adispersant and wetting agent and air-milling the blended mixture toeffect reduction of particle size to about the 5 to 10 micron range. Atypical wettable powder might contain 50% by weight of the phthalimidederivative, 5% by weight of a highly purified partially desulfonatedsodium lignin sulfonate, 1% by weight of sodium N-methyl-N-oleoyltaurateand 44% by weight of attapulgite.

In practice, it will also be found that the active ingredient in theabove formulation can be varied from about 25% to 80% by weight.However, in such cases, the solid diluent will have to be variedaccordingly.

For the preparation of a dust, for example a 10% dust, 20% by weight ofthe 50% wettable powder can be blended with about 80% by weight of asolid carrier, such as kaolin. Suitable equipment for such preparationsare ribbon-type blenders and double-cone blenders. It is also obviousthat the concentration of active ingredient in dust formulations can bereadily varied by adjusting the amount of wettable powder and carrierused. Typical dusts will generally vary between about 1% to 15% byweight of active ingredient, although higher concentrations may also beprepared.

An alternative process for preparation of dusts, also dust concentrates,involves blending the active phthalimide derivative with the solidcarrier and passing the uniform blend through an attrition mill toobtain the desired particle size.

A typical granular formulation can be prepared by blending a smallamount, i.e. about 0.3% by weight, of a fumed colloidal silica withabout 5.6% by weight of the phthalimido derivative and air-milling themixture to a uniform blend. Silica sand, about 85.7% by weight, is thenplaced in a blender along with about 0.7% by weight of calcium-sodiumlignin sulfonate powder and 4.2% of a 1% aqueous solution ofcalcium-sodium lignin sulfonate. The mixture is blended and then 3.5% byweight of synthetic calcium silicate is added. The mixture is permittedto continue blending for several minutes until the finished product isuniformly coated and free flowing. It is, of course, obvious that theamount of active ingredient in the formulated granular product can bewidely varied, preferably between about 1% to 15% by weight. This simplyrequires appropriate adjustment of the amount of granular carrier usedand/or adjuvants added. It is likewise obvious that sorptive granularcarriers, as well as non-sorptive carriers, can be employed in thepreparation of the granular formulation.

Other formulations, methods, products and advantages of the presentinvention may become apparent from the examples set forth below. Theseexamples are provided simply as an illustration of the invention and arenot intended to be limiting thereon.

EXAMPLE 1 Preparation of 1-(3-Chlorophthalimido)cyclohexanecarboxylicAcid ##SPC22##

Method A

A mixture containing 1 kg. 1-aminocyclohexanecarboxylic acid, 1.275 kg.3-chlorophthalic anhydride and 91 ml. triethylamine in 6.3 literstoluene is stirred and heated under reflux under a Dean-Stark waterseparator for 20 hours. During this time, 154 ml. of water arecollected. The solution is cooled to 0°C. to 5°C., and the product thencollected by filtration in a yield of 77%. This material has meltingpoint 193°C. to 194°C.

Method B.

An intimate mixture of 4.56 grams 3-chlorophthalic anhydride and 3.58grams 1-aminocyclohexanecarboxylic acid is heated at 210°C. until nomore water vapor is evolved. The cooled mixture is dissolved as far aspossible in boiling acetone, and the insolubles removed by filtration.The acetone is removed from the filtrate and the crystalline residuetransferred to a filter funnel with ether and air dried. The product isidentical to that described in Method A above.

Method C.

A mixture containing 91.3 grams 3-chlorophthalic anhydride and 71.6grams 1-aminocyclohexanecarboxylic acid in one liter acetic acid isheated under reflux for 21 hours. The solvent is then removed underreduced pressure, 250 ml. toluene added to the residue and the solventagain removed in vacuo. The residue is heated in one liter acetone andthe insolubles removed by filtration. The solvent is removed bydistillation, and the residue transferred to a filter funnel with etherand air dried. The product is identical to that prepared in Method Aabove.

Method D.

A mixture containing 9.13 grams 3-chlorophthalic anhydride and 7.16grams 1-aminocyclohexanecarboxylic acid in 100 ml. dimethylformamide isheated under reflux for 24 hours. The mixture is cooled, poured into icewater and the precipitated solid removed by filtration, washed withwater and air dried. Recrystallization of the solid from 95% ethanolwith filtration to remove insolubles gives the product identical to thatprepared by Method A.

The phthalimido acids of Table I, below, are prepared by the generalmethods described above. ##EQU3##

EXAMPLE 2 Preparation of 1-(3-Chlorophthalimido)cyclohexanecarbonylChloride ##SPC23##

In a 12 liter flask is placed 1.5 kg. of the1-(3-chlorophthalimido)cyclohexanecarboxylic acid and 7500 ml. benzene.The mixture is stirred and heated to boiling, and then 696 grams thionylchloride added dropwise. After the addition, heating is continued for 2hours. The volume of the solution is reduced by one-half, the solutionfiltered, and the remaining solvent removed under reduced pressure. Theacid chloride is used for the preparation of the carboxamides withoutfurther purification.

Using the procedure described above, the following acid chlorides areprepared from the corresponding acids described in Table II. These acidchlorides are used directly without further purification and arecharacterized only by their infrared spectrum. ##EQU4##

EXAMPLE 3 Preparation of 1-(3-Chlorophthalimido)cyclohexanecarboxamide##SPC24##

A solution containing the crude acid chloride prepared in Example 2 isdissolved in 8 liters of tetrahydrofuran and cooled to 10°C. to 15°C.Gaseous ammonia is bubbled through the stirred solution until an excessof ammonia begins escaping from the reaction flask. The mixture isstirred for a further 15 minutes and then filtered. The solids arewashed with water thoroughly to remove inorganic salts and the productis air dried. The tetrahydrofuran filtrate is evaporated under reducedpressure, and the residue combined with the air-dried solid and heatedto boiling in 3 liters toluene, cooled to 10°C. and the product removedby filtration to give 1.2 kg. product, melting point 194°C. to 195°C.

The carboxamides of Table III, below, are prepared by essentially thesame procedure as described above. ##EQU5##

EXAMPLE 4 Preparation of1-(3-Chlorophthalimido)-N,N-dimethylcyclohexanecarboxamide ##SPC25##

A solution containing 7.43 grams1-(3-chlorophthalimido)cyclohexanecarbonyl chloride in 50 ml.tetrahydrofuran is cooled to 10°C. to 15°C., and while stirring, gaseousdimethylamine is bubbled into the solution until saturated. After afurther 5 minutes, the mixture is filtered to remove salts and thesolvent removed from the filtrate. The residue is crystallized fromcyclohexane to give the product, melting point 135°C. to 137°C.

The N,N-dimethylcarboxamides of Table IV, below, are prepared usingessentially the same procedure described above.

                  TABLE IV                                                        ______________________________________                                                                              Melting                                                                       Point                                   X      X'    R.sub.1 R.sub.2                                                                            R.sub.3                                                                             R.sub.4                                                                             °C.                              ______________________________________                                        H      H     --(CH.sub.2).sub.5 --                                                                    CH.sub.3                                                                            CH.sub.3                                                                            112-113                                   3-NO.sub.2                                                                           H     --(CH.sub.2).sub.5 --                                                                    CH.sub.3                                                                            CH.sub.3                                                                            132.5-134.5                               ______________________________________                                    

EXAMPLE 5 Preparation of 1-(3-Chlorophthalimido)cyclohexanecarboxylicAcid, 2,2-Dimethylhydrazide ##SPC26##

To an ice-cold solution of acid chloride in tetrahydrofuran is addeddropwise two equivalents of 1,1-dimethylhydrazine. After stirring afurther 0.5 hour, the solids are removed by filtration and the solventremoved in vacuo from the filtrate. The residue is crystallized fromacetonitrile to give the product, melting point 184°C. to 185°C.

EXAMPLE 6 Preparation of2-[1-(3-Chlorophthalimido)cyclohexylcarbonyl]-1,1,1-trimethylhydraziniumChloride. ##SPC27##

To the dimethylhydrazide prepared as described in Example 5 intetrahydrofuran is added excess methyl iodide and the mixture heatedunder reflux for 4 hours. The solids are removed by filtration and airdried to give the quaternary iodide. The iodide is converted to thechloride by passing a 50% aqueous ethanol solution of the salt slowlydown a column packed with Amberlyst A21, an organic ion exchange resin,in its chloride form and evaporating the eluent. The residue iscrystallized from ethanol-ether to give the chloride salt, melting point202°C. to 203°C.

EXAMPLE 7 Preparation of Ethyl and Methyl1-(3-Chlorophthalimido)cyclohexanecarboxylate ##SPC28##

An excess of an ether solution of diazoethane is added to a solution of1-(3-chlorophthalamido)cyclohexanecarboxylic acid in tetrahydrofuran.After standing for one hour at room temperature, the solution is washedwith excess aqueous sodium carbonate solution, followed by two waterwashes. The organic phase is dried and the solvent evaporated underreduced pressure. The residue is crystallized from hexane to give theester, melting point 70°C. to 71°C.

Alternatively, this ester can be prepared by the action of ethanol andpyridine on the acid chloride, described in Example 2.

Methyl 1-(3-chlorophthalamido)cyclohexanecarboxylate is prepared byheating 5.7 g. or 3-chlorophthalic anhydried with 4.9 g. methyl1-aminocyclohexanecarboxylate in 100 ml. toluene containing 2 ml.triethylamine under a Dean-Stark separator for 24 hours. The solvent isremoved under reduced pressure and the residue dissolved as far aspossible in ether. The product crystallized from a mixture of ether andhexane to give 5.7 g. methyl ester, m.p. 90°-92°C.

EXAMPLE 8 Preparation ofα-(3-Chlorophthalimido)-α-isopropyl-α-methylacetonitrile ##SPC29##

To 60 ml. dry tetrahydrofuran, stirred and cooled to 0°C. is addeddropwise 11.5 ml. titanium tetrachloride in 15 ml. dry carbontetrachloride. To this cold mixture is added 8.82 grams ofα-(3-chlorophthalimido)-α-isopropyl-α-methylacetamide in 50 ml. drytetrahydrofuran, followed by 12.3 grams triethylamine in 20 ml. drytetrahydrofuran. The reaction mixture is allowed to warm slowly to roomtemperature and kept overnight. Water is then added cautiously to themixture while it is extracted three times with ether. The combinedextracts are washed with water, dried, and evaporated. The residue iscrystallized from ether-hexane to give 6.1 grams of the nitrile, meltingpoint 71°C. to 72°C.

The starting amide can be dehydrated by other reagents, such asphosphorus pentoxide and phosphorus oxychloride in benzene, aceticanhydride and trifluoroacetic anhydride to yield the same product.

EXAMPLE 9 Preparation of2,2-Disubstituted-2-(3,4,5,6-tetrahydrophthalimido)acetic acids##SPC30##

Using the procedure set forth in Example 1 but substituting3,4,5,6-tetrahydrophthalic anhydride for 3-chlorophthalic anhydrideaffords the compounds set forth in Table V.

                  Table V                                                         ______________________________________                                        R.sub.1                                                                             R.sub.2      Solvent  Method                                                                              Melting Point                               ______________________________________                                        (CH.sub.2).sub.5                                                                             Xylene   A       134-136°                               --(CH.sub.2).sub.4 --                                                                        Xylene   A       86-87°                                 --(CH.sub.2).sub.6 --                                                                        Xylene   A       Oil                                           CH.sub.3                                                                            --CH.sub.2 CH(CH.sub.3).sub.2                                                              Xylene   A     118-119.5°                           CH.sub.3                                                                            --CH(CH.sub.3).sub.2                                                                       Xylene   A     Oil                                         ______________________________________                                    

EXAMPLE 10 Preparation of2,2-Disubstituted-2-(3,4,5,6-tetrahydrophthalimido)acetyl chloride

Using the procedure set forth in Example 2 but substituting the acidslisted in Table V and Example 9 for 1-(3-chlorophthalimido)cyclohexanecarboxylic acid, the acid chlorides listed in Table VI areprepared. These acid chlorides are obtained as oils and used directlywithout further purification and are characterized only by theirinfrared spectra.

                  Table VI                                                        ______________________________________                                        R.sub.1          R.sub.2                                                      ______________________________________                                        --(CH.sub.2).sub.5 --                                                         --(CH.sub.2).sub.4 --                                                         --(CH.sub.2).sub.6 --                                                         CH.sub.3         CH.sub.2 CH(CH.sub.3).sub.2                                  CH.sub.3           CH(CH.sub.3).sub.2                                         ______________________________________                                    

EXAMPLE 11 Preparation of2,2-Disubstituted-2-(3,4,5,6-tetrahydrophthalimido)acetamides

Using the procedure set forth in Example 3 but substituting the acidchlorides listed in Table VI for 1-(3-chlorophthalimido)cyclohexanecarbonyl chlorides, the amides listed in Table VII areprepared.

                  Table VII                                                       ______________________________________                                                             Melting                                                  R.sub.1                                                                              R.sub.2       Point °C                                          ______________________________________                                        --(CH.sub.2).sub.5 --                                                                          203-204                                                      --(CH.sub.2).sub.4 --                                                                          172-173                                                      --(CH.sub.2).sub.6 --                                                                          133-134                                                      CH.sub.3                                                                             --CH.sub.2 CH(CH.sub.3).sub.2                                                               129-130                                                  CH.sub.3                                                                               --CH(CH.sub.3).sub.2                                                                      142.5-143.5                                              ______________________________________                                    

EXAMPLE 12 Preparation of1-(1,2,3,6-Tetrahydrophthalimido)-1-cyclohexanecarboxylic acid

Using the procedure set forth in Example 1 but substituting1,2,3,6-tetrahydrophthalic anhydride for 3-chlorophthalic anhydride, thefollowing compound is prepared. ##SPC31##

EXAMPLE 13 Preparation of1-(1,2,3,6-Tetrahydrophthalimido)-1-cyclohexanecarbonyl chloride

Using the procedure set forth in Example 2 but substituting the acid ofExample 12 for 1-(3-chlorophthalimido) cyclohexanecarboxylic acid, theacid chloride shown below is prepared. This acid chloride is useddirectly without further purification and is characterized only by theinfrared spectra ##SPC32##

EXAMPLE 14 Preparation of1-(1,2,3,6-Tetrahydrophthalimido)-1-cyclohexanecarboxamide

Using the procedure set forth in Example 3 but substituting the acidchloride from Example 13 for 1-(3-chlorophthalimido) cyclohexanecarbonylchloride, gives the amide listed below.

Table VIII ##SPC33##

Melting point: 192°-194°C.

EXAMPLE 15 Preparation of Methyl1-(3,4,5,6-tetrahydrophthalimido)-1-cyclohexanecarboxylate ##SPC34##

A mixture containing 11.4 g 1-cyclohexene-1,2-dicarboxylic acidanhydride, 11.8 g. methyl 1-aminocyclohexanecarboxylate andtriethylamine in 150 ml toluene was heated under reflux under aDean-Stark water trap overnight. Removal of the solvent left an oilwhich was purified by chromatography on magnesium silicate to give thecrystalline, ester, m.p. 44°-45°C.

EXAMPLE 16 Preparation of1-(3,4,5,6-Tetrahydrophthalimido)-1-cyclohexanecarbonitrile ##SPC35##

Using the procedure described in Example 8 but substituting1-(3,4,5,6-tetrahydrophthalimido)-1-cyclohexanecarboxamide forα-(3-chlorophthalimido)-α-isopropyl-α-methylacetamide, the titlecompound is formed, m.p. 55.5°-56.5°C.

EXAMPLE 17 Preparation of1-(3-chlorophthalimido)-N-methyl-1-cyclohexanecarboxamide ##SPC36##

Using the same procedure as described in Example 3 but replacing theammonia with methylamine gives the title mono-methylamide, m.p.168.5°-170°C. Similarly, reacting1-(3-acetamidophthalimido)-cyclohexanecarbonyl chloride with methylamineyields 1-(3-acetamidophthalimido)-N-methylcyclohexanecarboxamide, m.p.205°-207.5°C.

EXAMPLE 18 Preparation of4'-Chloro-1-(3-methylphthalimido)-1-cyclohexanecarboxanilide ##SPC37##

To a solution containing 13.16 g. of the acid chloride described inTable II in 125 ml. tetrahydrofuran was added dropwise with stirring atroom temperature a solution containing 11.0 g. p-chloroaniline in 75 ml.tetrahydrofuran. After a further 0.5 hour, the mixture was filtered, thefiltrate evaporated and the residue crystallized from acetonitrile togive the desired carboxanilide m.p. 208.5°-209°C.

EXAMPLE 19 Preparation of 1-(hexahydrophthalimido)cyclohexanecarboxylicacids

Using the procedure described in Example 1 but substituting cyclohexane-1,2-dicarboxylic anhydride and 4-methylcyclohexane-1,2-dicarboxylicanhydride for 3-chlorophthalic anhydride, the hexahydrophthalimidocompounds in Table IX are prepared.

                  Table IX                                                        ______________________________________                                                                        Melting                                                                       Point                                         W        Solvent     Method     °C                                     ______________________________________                                        H        Toluene     A          135-136                                       CH.sub.3 Xylene      A          92-97                                         ______________________________________                                    

EXAMPLE 20 Preparation of 1-(hexahydrophthalimido)cyclohexanecarbonylchlorides

Using the procedure described in Example 2 but substituting the acidslisted in Table IX for 1-(3-chlorophthalimido)cyclohexanecarboxylicacid, the acid chlorides listed in Table II are prepared. These acidchlorides were characterized only by their infrared spectra and werethen converted directly to the amides listed in Table X.

Table X ##SPC38##

W = h or 4-CH₃

EXAMPLE 21 Preparation of1-(hexahydrophthalimido)cyclohexanecarboxamides

Using the procedure described in Example 3 but substituting the acidchlorides listed in Table X for 1-(3-chlorophthalimido)cyclohexanecarbonyl chloride, the amides listed in Table XI areprepared.

                  Table XI                                                        ______________________________________                                        W         Melting Point °C                                                                         CL No.                                            ______________________________________                                        H         186-188           99,488                                            4--CH.sub.3                                                                             150-152           99,622                                            ______________________________________                                    

EXAMPLE 22 Preparation of 3(or6)-Chloro-N-(1-cyanocyclohexyl)-phthalamic acid ##SPC39##

A mixture containing 18.26 g. 3-chlorophthalic anhydride and 12.4 g.1-aminocyclohexanecarbonitrile in 250 ml. ether is heated under refluxfor 2 hours. The mixture was cooled and the crystalline solid productremoved by filtration. The 3(or6)-chloro-N-(1-cyanocyclohexyl)-phthalamic acid may be recrystallizedfrom acetone/hexane to give analytically pure material m.p. 154°-155°C.

Similarly, when phthalic anhydride is subsituted for 3-chlorophthalicanhydride, the product, N-(1-cyanocyclohexyl)-phthalamic acid, m.p.154.5°-156°C. is formed.

EXAMPLE 23 Preparation of 3-Chloro-N-(1-cyanocyclohexyl)-phthalimide##SPC40##

A slurry of 1.5 g. of 3(or 6)-chloro-N-(1-cyanocyclohexyl)-phthalamicacid in 10 ml. acetic anhydride is heated at reflux for 4 hours. Theanhydride is removed by evaporation at reduced pressure to leave acrystalline residue. The residue is recrystallized from isopropanol togive analytically pure 3-chloro-N-(1-cyanocyclohexyl)-phthalimide, m.p.153.5°-154.5°C.

Similarly, when 3(or 6)-chloro-N-(1-cyanocyclohexyl)-phthalamic acid isreplaced by N-(1-cyanocyclohexyl)phthalamic acid the product,N-(1-cyanocyclohexyl)-phthalimide, m.p. 115°-116.5°C. is formed.

EXAMPLE 24 Preparation of 1-(3-Chlorophthalimido)cyclohexanecarboxamide##SPC41##

To a solution containing 300 mgs.3-chloro-N-(1-cyanocyclohexyl)-phthalimide in 3ml. methylene chloride isadded, with good stirring, 0.38 ml. concentrated sulfuric acid. After0.5 hour, ice is added and the aqueous phase extracted with chloroform.The organic phase is washed with water, dried and evaporated to give the1-(3-chlorophthalimido)cyclohexanecarboxamide which can be purified byrecrystallization from aqueous ethanol, m.p. 193°-194°C.

EXAMPlE 25 Preparation of 3-Trichloromethylphthalic Anhydride ##SPC42##

Into a stirred, molten mass of 45.85 g. of 3-methylphthalic anhydride at145°C. is slowly passed chlorine gas while the reaction mixture isirradiated with a sun lamp. After four hours, the temperature isincreased to 170°C. The temperature is further increased as follows:after six and one-half hours, 190°C., and after fourteen and one-halfhours, 230°C., after a total of eighteen hours. The reaction mixture isallowed to cool to 100°C. Sixty ml of toluene is then added, and thesolution is transferred to an erlenmeyer flask. It is then diluted with60 ml of toluene plus 60 ml of hexane, followed by warming to affectsolution, and cooling to precipitate the product. The resulting crystalsare removed by filtration and washed with cold hexane leaving 65 g of atan solid, m.p. 121°-124°C.

EXAMPLE 26 Preparation of 3-Trifluoromethylphthalic Anhydride ##SPC43##

A mixture of 12.43 g of 3-trichloromethylphthalic anhydride, 12.5 g ofantimony trifluoride, and a few grams of sand are heated at 200°C. Themolten mass is stirred for one hour. It is then cooled, stirred withbenzene and water, and the mixture filtered and separated. The resultingorganic solution is washed with water and brine, dried, and the solventevaporated leaving 7.29 g. of a brown solid, m.p. 65°-67°C.

EXAMPLE 27 Preparation of1-(3-trifluoromethylphthalimido)cyclohexanecarboxamide ##SPC44####SPC45##

Equal weights of the trichloromethyl derivative and antimony trifluorideare heated together at 200° with some sand for 1 hour. The mixture iscooled, stirred with some sand for 1 hour. The mixture is cooled,stirred with toluene and water, the mixture filtered and the organicphase separated. The organic phase is washed with water and brine, driedand the solvent evaporated to give the trifluoromethyl derivative whichcan be recrystallized from nitromethane, m.p. 166°-167°C.

Alternatively the same product can be obtained from thetrifluoromethylphthalic anhydride using the methods described inExamples 1-3.

EXAMPLE 28 Preparation of1-(3-dimethylaminophthalimido)cyclohexanecarboxamide ##SPC46##

Reductive alklation of 1-(3-nitrophalimido) cyclohexanecarboxamide iscarried out with formaldehyde and hydrogen in the presence of platinummetal catalyst at room temperature in ethanol to give the titlecompound, m.p. 166.5° - 169°C.

EXAMPLE 29 Preparation of a mixture of 1-(3- and4-chlorophthalimido)cyclohexanecarboxamide ##SPC47##

A mixture containing 14.0 g mixed chloroxylenes (approx. 55%4-chloroxylene and 45% 3-chloroxylene) in 400 ml water containing 69 gpotassium permanganate is heated under reflux for 4 hours. The mixtureis filtered and the filtrate acidified with conc. H₂ SO₄ to pH 1.Evaporation of the water leaves a solid residue which is extracted intoa 1:1 mixture of chloroform: isopropanol. Evaporation of the solventleaves the mixed 3- and 4-chlorophthalic acids m.p. 115°C. (decomp).

The mixed chlorophthalic acids are heated in 50 ml acetic anhydride forone hour, the solvent is removed to give the mixed 3- and4-chlorophthalic anhydrides m.p. 52°-66°C.

Condensation of the mixed anhydrides with 1-aminocyclohexanecarboxylicacid as described in Example 1 gives the mixed 1-(3- and4-chlorophthalimido)cyclohexanecarboxylic acids m.p. 166°-177°C. which,when reacted with thionyl chloride in benzene as described in Example 2,gives the mixed 1(3- and 4-chlorophthalimido)cyclohexanecarbonylchlorides as an oil. The reaction of the above-described carbonylchlorides with ammonia as described in Example 3, gives the desiredmixture named in the title, m.p. 167°-175°C.

EXAMPLE 30 Preparation of 1-(3-bromophthalimido)cyclohexanecarboxamide##SPC48##

A solution of 1-(3,4-dibromophthalimido)cyclohexanecarboxamide in aceticacid containing one equivalent of sodium acetate is reduced withhydrogen in the presence of palladium on carbon to give the product1-(3-bromophthalimido) cyclohexanecarboxamide, m.p. 199°-200°C.

EXAMPLE 31 Preparation of 3-benzyloxy-6-methylphthalic anhydride##SPC49## ##SPC50##

To a stirred solution containing 25.2 g phenol in 250 ml dry t-butanolwas added 11.2 g potassium t-butoxide in a nitrogen atmosphere. After 15minutes, 17.1 g benzyl bromide is added dropwise. The reaction isstirred overnight and then poured into water and the product extractedinto ether. The extract is washed successively with water, cold 2N NaOH,water and brine, dried and the solvent evaporated to leave 32.9 g ofcrude diethyl 3-benzyloxy-6-methyl phthalate.

The crude ester is heated under reflux for 3 hours in 150 ml water and100 ml 95% ethanol containing 20 g NaOH. The mixture is poured intowater and the resulting solid removed by filtration, washed with waterand air-dried to give 24.4 g crude 3-benzyloxy-6-methylphthalic acid.

The crude phthalic acid prepared above is heated in 150 ml aceticanhydride for two hours. The solvent is removed under reduced pressureand the crystalline residue collected and washed with ether. Theanhydride may be recrystallized from nitromethane to give an analyticalsample m.p. 200°-203°C.

EXAMPLE 32 Preparation of1-[3-(ethylsulfonyl)-6-methylphthalimido]-cyclohexanecarboxylic acid##SPC51##

To a solution of 15.6 g 30% hydrogen peroxide in 15 ml acetic acid isadded 8.9 g of the sulfide in 80 ml acetic acid and the mixture heatedunder reflux for 1.5 hours. The volume of the solution is reduced bythree quarters and the residue is poured into water. The product isextracted into ether, washed with water, the organic phase dried and thesolvent evaporated. The residue is crystallized from benzene to give theethylsulfonyl derivative with m.p. 152°-153°C.

EXAMPLE 33 Preparation of1-(3-hydroxy-6-methylphthalimido)-cyclohexanecarboxamide ##SPC52##

A solution containing 2.7 g of the benzyl ether in 100 ml acetic acid isshaken in an atmosphere of hydrogen in the presence of 2 g 5% palladiumon carbon. The hydrogenation is complete in 20 minutes and the catalystis removed by filtration and the filtrate evaporated to give 500 mgproduct. The filter cake is washed with dimethylformamide and thefiltrate poured into water. The precipitate is removed by filtration,washed with water and air-dried to give a further 800 mg product.Recrystallization of the combined fractions from acetic acid gaveanalytically pure product, m.p. 265°C. (decomp).

EXAMPLE 34 Plant Growth Regulating Effects of Phthalimido Derivatives ona Variety of Plant Species

In these tests, a 50/50 water/acetone mixture containing1-(3-chlorophthalimido)cyclohexanecarboxamide is sprayed on the soilsurface of 2 square foot flats in sufficient amount to provide 4 poundsper acre of active compound. Seeds of a variety of plants are thenplaced on the treated soil and covered with untreated soil to a depth ofone inch. The planted flats are then placed on greenhouse benches,watered and maintained in accordance with normal greenhouse practices.All tests are run in duplicate and untreated flats are used as controls.

All flats are examined periodically and the results observed andrecorded. The plant species used are indicated below in Table XII alongwith emergence times and plant height for each species. All tests areterminated 28 days after planting.

                  TABLE XII                                                       ______________________________________                                               Plant Species Employed                                                 ______________________________________                                        Cotton Corn (Sweet)  Sugar beet    Celery                                     Pea    Wheat         Soybean       Sudangrass                                 Sorghum                                                                              Tomato        Alfalfa       Peanut                                     Rape   Navy Bean     Rice          Safflower                                  Oat    Lima Bean     Radish        Cabbage                                    Cucumber                                                                             Potato        Birdsfoot trefoil                                                                           Snap bean                                  Flax   Barley        Carrot        Lettuce                                    ______________________________________                                        Emergence Times                                                               Emerged in      Treated Plants                                                ______________________________________                                        3 days     Radish and Alfalfa                                                 4 days     Barley and Soybean, Cucumber, Sugar beet,                                     Sudangrass, Wheat, Rape, Pea                                       5 days     Flax, Corn, Safflower, Oat, Navy bean,                                        Cotton, Lima bean, Cabbage, Snap bean,                                        Birdsfoot trefoil                                                  6 days     Sorghum, Tomato, Potato                                            7 days     Peanut, Lettuce, Rice, Carrot                                      12 days    Celery                                                             ______________________________________                                        Emerged in  Control Plants                                                    ______________________________________                                        6 days     Cotton, Soybean                                                    7 days     Navy bean, Snap bean                                               8 days     Tomato                                                             10 days    Potato                                                             15 days    Celery                                                             ______________________________________                                        Remaining plants emerged at the same time as treated plants.                  Observed Plant Height 28 Days After Treatment                                 ______________________________________                                        Plants 50% or More Taller than Controls                                       ______________________________________                                        Potato     Soybean      Oats    Sugar beet                                    Lettuce    Cucumber     Rice    Cotton                                        Lima bean  Wheat        Corn    Flax                                          Snap bean  Barley       Tomato  Rape                                          ______________________________________                                        Plants 25% to 50% Taller than Controls                                        ______________________________________                                        Radish         Sudangrass      Sorghum                                        Carrot         Cabbage         Navy bean                                      Safflower      Pea             Peanuts                                        ______________________________________                                        Plants Approximately the Same Height as Controls                              ______________________________________                                        Alfalfa                                                                       Birdsfoot trefoil                                                             Celery                                                                        ______________________________________                                    

EXAMPLE 35 Plant Growth Regulating Effect of Phthalimido Derivatives onXanthia Tobacco

In this test, untopped tobacco plants of approximate similar height aretreated with 50/50 acetone/water mixtures containing 100 ppm., 200 ppm.,or 400 ppm. of 1-(3-chlorophthalimido)cyclohexanecarboxamide and thenplaced on greenhouse benches. All treatments are replicated four timesand untreated plants are used as controls. Twenty-eight days aftertreatment, all plants are examined and measured.

Data obtained are reported below in TAble XIII, where it can be seenthat plants treated with 100 ppm. of test compound have an 18% gain overcontrols and those treated with 200 ppm. and 400 ppm. show 28% and 50%gains, respectively, over controls.

Five weeks after treatment, the tallest and shortest plants from eachtreatment are cut and weighed and the average weight per treatmentdetermined. From the data, it can be seen that the percent gain oftreated plants over untreated controls is from 30% to 70%.

The dry weights of the two middle plants in the four replicates is takennine weeks after treatment and shows a 12% to 54% increase overuntreated controls. These data are given below in Table XIII.

                                      TABLE XIII                                  __________________________________________________________________________    Xanthia Tobacco                                                                          Height in Inches at Rates of:                                                                            Control                                            400 ppm. 200 ppm. 100 ppm. Acetone/Water                           Compound   (16 mg./Plant)                                                                         (8 mg./Plant)                                                                          (4 mg./Plant)                                                                          50/50                                   __________________________________________________________________________    1-(3-Chlorophthal-                                                            imido)cyclohexane-                                                            carboxamide                                                                   Replicate I                                                                              35       28       24.5     23                                           II    33       28       27       23                                           III   33       30       29       26                                           IV    37       32       28.5     20                                      Average    34.5     29.5     27.2     23                                      __________________________________________________________________________               % Gain Over                                                                   Controls at Rates of:                                              Compound   400 ppm.                                                                            200 ppm.                                                                            100 ppm.                                               __________________________________________________________________________    1-(3-Chlorophthal-                                                            imido)cyclohexane-                                                            carboxamide                                                                              +50%  +28%  +18%                                                   __________________________________________________________________________    Xanthia Tobacco                                                                          Wet Weights in Grams                                                          of Two Replicates                                                             (The Tallest and the Smallest)                                                                  Control                                                     at Treatment Rates of:                                                                          Acetone/Water                                    Compound   400 ppm.                                                                            200 ppm.                                                                            100 ppm.                                                                            50/50                                            __________________________________________________________________________    1-(3-Chlorophthal-                                                            imido)cyclohexane-                                                            carboxamide                                                                   Replicate I                                                                              111    84   100   75                                                    II    151   114   115   77                                               Average    131     99   107.5                                                                              76                                               __________________________________________________________________________               % Gain Over Controls                                                          in Wet Weight at Rates of:                                         Compound   400 ppm.                                                                            200 ppm.                                                                            100 ppm.                                               __________________________________________________________________________    1-(3-Chlorophthal-                                                            imido)cyclohexane-                                                            carboxamide                                                                              +72%  +30%  +41%                                                   __________________________________________________________________________    Treated plants were taller than untreated plants, but they                    did not have more leaves. The internodal spaces were elongated,               yet the stems did not appear to be thinner than the checks.                   Xanthia Tobacco                                                                          Dried Weights in Grams                                                        of Two Replicates                                                             (Two Middle Plants)                                                                             Control                                                     at Treatment Rates of                                                                           Acetone/Water                                    Compound   400 ppm.                                                                            200 ppm.                                                                            100 ppm.                                                                            50/50                                            __________________________________________________________________________    1-(3-Chlorophthal-                                                            imido)cyclohexane-                                                            carboxamide                                                                              31.5  23    26.5  20.5                                             __________________________________________________________________________               % Gain Over Controls                                                          in Dry Weight at Rates of:                                         Compound   400 ppm.                                                                            200 ppm.                                                                            100 ppm.                                               __________________________________________________________________________    1-(3-Chlorophthal-                                                            imido)cyclohexane-                                                            carboxamide                                                                              +53.6%                                                                              +12.2%                                                                              +29%                                                   __________________________________________________________________________

EXAMPLE 36 Seed Treatment to Improve Fresh Weights and Dry Weights ofPlants.

In these tests, seeds of field corn (DeKalb XL-45) are soaked for 2hours in water or an aqueous solution containing 10 ppm., 100 ppm. or1000 ppm. of 1-(3-chlorophthalimido)cyclohexanecarboxamide. After suchtreatment, the seeds are planted, five per pot, in 5-inch plastic potsand placed in the greenhouse where they are cared for in accordance withstandard greenhouse procedures.

Three weeks after treatment, all plants are measured, harvested andweighed. After weighing, the harvested plants are dried and dry weightsfrom each treatment determined. Data obtained are given below in TableXIV, where it can be seen that about a 20% to 36% increase in height,15% to 28% increase in fresh weight, and a 5% to 21% increase in dryweight of treated plants is obtained.

                                      TABLE XIV                                   __________________________________________________________________________    Seed Treatment to Improve Fresh Weight, Height and Dry Weight of Field        Corn                                                                          Test Compound = 1-(3-Chlorophthalimido)cyclohexanecarboxamide                        Fresh Weights      Dry Weights           % Change                             of Tops in Grams   of Tops in Grams      Fresh Wt.                                                                             Dry Wt.               Treatment                                       Average                                                                               Average 3             Rates  Replicate I                                                                         Replicate II                                                                        Replicate III                                                                        Replicate I                                                                          Replicate II                                                                         Replicate III                                                                         Replicates                                                                            Replicates            __________________________________________________________________________    0 ppm. 14.8  19.5  20.1  1.70  2.05    1.90     --      --                    10 ppm.                                                                              20.9  21.3  20.8  2.00  2.02    1.94     +15      +5                   100 ppm.                                                                             22.0  24.5  21.9  2.18  2.21    2.18     +26     +16                   1000 ppm.                                                                            23.2  25.3  21.5  2.24  2.26    2.33     +28     +21                   __________________________________________________________________________           Height (cm.) to    Total Height          % Change                             Second Leaf        (cm.)                                               Treatment                                       Second Leaf                                                                           Total                 Rates  Replicate I                                                                         Replicate II                                                                        Replicate III                                                                        REplicate I                                                                          Replicate II                                                                         Replicate III                                                                         Average Average               __________________________________________________________________________    0 ppm.  9     9     9     30     37     32      --      --                    10 ppm.                                                                              10    12    10     38     41     37      +19     +18                   100 ppm.                                                                             10    13    11     39     42     40      +25     +21                   1000 ppm.                                                                            12    13    12     43     45     42      +36     +30                   __________________________________________________________________________

EXAMPLE 37 Plant Growth Regulating Effects of Phthalimido Derivatives

In these tests, seeds and seed pieces of tomato and potato,respectively, are placed in rows on a soil surface in flats. A spray,50/50 acetone/water containing the test compound, is applied over theseed and soil surface in sufficient amount to provide 0.5, 1, 2 or 4pounds per acre of test compound. The seed is covered with aboutone-half inch of untreated soil and watered. The flats are placed ongreenhouse benches and cared for in accordance with greehouse practices.Three weeks after treatment, the flats are examined and the height andfresh weight of the tomato and potato plants determined. The number ofstems on the potato plants are also counted since the number of stemsper plant is an indication of the number of potatoes that will be set.Data obtained are reported below in Table XV.

                                      TABLE XV                                    __________________________________________________________________________    Plant Growth Regulating Effects of Test Compounds                                              Tomato            Potato                                                                Grams                                                               Rate  Weight                                                                            5 Plants                                                                              Height                                                                            Number of                                                                           Fresh Weight                     Compound         lbs./acre                                                                           cm. Fresh Weight                                                                          cm. Stems Grams                            __________________________________________________________________________    2-[1-(3-chlorophthalimido)-                                                                    1/2   11  8       20  24    109                               cyclohexylcarbonyl]-                                                                          1     12  9       21  23    124                               1,1,1-trimethylhydrazinium                                                                    2     11  9.5     21  21    130                               chloride        4     11  10.5    25  21    181                              1-(3-chlorophthalimido)-                                                                       1/2   17  17      32  16    134                               cyclohexanecarboxamide                                                                        1     --  --      33  13    109                                               2     17  15.5    34  25    147.5                                             4     16  10.5    36  19    104                              α-(3-chlorophthalimido)-α-                                                         1/2   11  10      23  19    145                               methyl-α-150 propylacetamide                                                            1     10  9.5     21   9    85.5                                              2      7  3       19   7    30                                                4      6  1.5     13   2    22                               1-(3-chlorophthalimido)-                                                                       1/2    8  7       22  19    155                               cycloheptanecarboxamide                                                                       1      8  8.5     18  13    65.5                                              2     11  14.5    20  21    122                                               4      6  4       22  22    145                              1-(3-chlorophthalimido)-                                                                       1/2   11  12.5    19  18    153                               2,2-dimethylhydrazide                                                                         1     12  13      19  15    137                               cyclohexanecarboxylic acid                                                                    2     12  14.5    21  19    179                                               4     12  14.5    24  12    123.5                            1-(3-chlorophthalimido)-                                                                       1/2   12  16.5    18  14    113.5                             cyclopentanecarboxylic acid                                                                   1     11  14      18  19    95.5                                              2     12  12      20  26    149.5                                             4     10  12      18  20    139.0                            α-(3-chlorophthalimido)-α-                                                         1/2   15  14.5    17  16    84.5                              isobutyl-α-methylacetamide                                                              1     15  17.5    24  19    188                                               2     15  13.0    24  16    98.5                                              4     13  11.0    26  20    177                              1-(3-nitrophthalimido)-                                                                        1/2   12  12.5    25  17    146.5                             cyclohexanecarboxylic acid                                                                    1     13  10.0    22  18    182.5                                             2     13  12.5    27  13    170.5                                             4     15  13.0    21  11    150.5                            α-(3-nitrophthalimido)-α-                                                          1/2   14  15.0    23  26    182                               isobutyl-α-methylacetamide                                                              1     10  11.5    20  21    141                                               2     11  11.5    21  16    117                                               4      9  7.5     23  19    174                              1-(3-chlorophthalimido)-                                                                       1/2   10  11.5    22  20    152                               cyclohexanecarboxylic acid                                                                    1      7  7.0     21  17    144                               ethyl ester     2     12  10.0    23  15    143                                               4     10  8.5     22  13    98                               N,N-dimethyl-1-(3-nitro-                                                                       1/2     8 6       19  19    135.5                             phthalimido)cyclohexane-                                                                      1      9  9.5     23  18    192                               carboxamide     2     12  11.0    23  13    141                                               4     11  9.5     21  29    160.5                            1-(3-chlorophthalimido)-                                                                       1/2   13  12.0    22  19    138                               N,N-dimethyl cyclohexane-                                                                     1     12  12.5    18  19    119                               carboxamide     2     10  8.5     21  17    159                                               4     10  12.5    21  15    145                              1-(3-nitrophthalimido)-                                                                        1/2   13  13.0    20  18    169                               cyclohexanecarboxamide                                                                        1     11  13.5    18  14    111.5                                             2     12  13.0    20  22    152                                               4     10  10.0    19  21    132.5                            1-(3-chlorophthalimido)-                                                                       1/2   14  14.5    26  27    212                               cyclopentanecarboxamide                                                                       1     11  9.5     23  17    124.5                                             2     12  12.0    30  23    204                                               4     12  11.5    32  15    140                              1-(3-chlorophthalimido)-                                                                       1/2   10  7.5     19  18    142.5                             cycloheptanecarboxylic acid                                                                   1     10  7.0     24  15    197                                               2     11  10.0    20  17    121.5                                             4     10  13.5    25  18    184                              1-phthalimidocyclohexane-                                                                      1/2   13  18.0    11  14    62                                carboxylic acid 1     12  9.5     22  13    111                                               2     12  14.0    24  13    111                                               4     11  10.5    23  16    142.5                            1-phthalimidocyclohexane-                                                                      1/2    7  6.0     22  14    80.5                              carboxamide     1      6  5.0     24  16    148.5                                             2     10  9.0     20  17    75.5                                              4     10  7.0     26  17    76.5                             1-phthalimidocyclopentane-                                                                     1/2   10  11      13  14    33.5                              carboxamide     1      8  7.5     19  17    118.5                                             2     11  11.5    27  22    121.5                                             4     10  10.0    28  14    135.5                                Controls                                                                  Average of 6 Replications                                                     3 Water & 3 Acetone/Water                                                                      --    10.6                                                                              12      19.5                                                                              17.3  122.6                            __________________________________________________________________________

EXAMPLE 38 Effect of 1-(3-Chlorophthalimido)cyclohexanecarboxamide onPotatoes

In these tests, potato seed pieces are placed on the surface of soil indeep flats approximately 2 feed square and sprayed with an aqueoussolution of test compound in a 50/50 acetone/water mixture. Applicationsare sufficient to provide from 0 to 4 pounds per acre of activecompound, and after spraying the seed pieces are covered with soil. Theflats are placed in the greenhouse and cared for in accordance withnormal greenhouse procedures. Eight weeks after treatment, the plantswith roots and tubers are harvested and examined. From the dataobtained, which is reported below in Table XVI, it can be seen that theshoots of treated plants are taller, stronger and weigh more thanuntreated controls. The number of shoots increases 16% to 33%, the rootsare heavier, and the number of tubers initiated are higher.

                  TABLE XVI                                                       ______________________________________                                        Potato Yield                                                                  Compound Used in These Tests                                                  1-(3-Chlorophthalimido)cyclohexanecarboxamide                                 Shoots                  Tubers  Roots                                         Treatment        Height   Weight        Weight                                ppm.    Number   cm.      gram    Number                                                                              gram                                  ______________________________________                                        Control 6        41       126.2    9    77.2                                  10      6        49       147.8    9    100.5                                 100     7        48       123.0   10    91.1                                  1,000   7        64       134.6    9    101.0                                 10,000  8        96       138.4   19    118.7                                 Control 5        51       111.2    8    82.7                                  10      7        52       144.2   11    123.5                                 100     6        56       119.0    9    83.7                                  1,000   8        73       155.4   15    108.8                                 10,000  8        100      181.8   22    106.7                                 ______________________________________                                    

EXAMPLE 39 Improved Stem Strength in Xanthia Tobacco and Effect on PlantHeight and Leaf Number

In the following tests, Xanthia tobacco plants approximately two monthsold and growing in individual pots are treated at first flowering withan aqueous/acetone (50/50) mixture containing 100 ppm. to 1600 ppm. or800 ppm. to 3200 ppm. of 1(3-chlorophthalimido)cyclohexanecarboxamide.One month after treatment, the plants are examined and the stemsharvested to determine the dry weights thereof or the number of leavescounted and the plants measured. Data obtained are provided below inTable XVII.

                                      TABLE XVII                                  __________________________________________________________________________    Xanthia Tobacco                                                                          Dried Weights of Tobacco Stems in Grams                                       (4 Replicates)                 Control                             Compound   1600 ppm.                                                                            800 ppm.                                                                            400 ppm.                                                                            200 ppm.                                                                            100 ppm.                                                                            0                                   __________________________________________________________________________    1-(3-chlorophthal-                                                             imido)cyclohexane-                                                            carboxamide                                                                             74      86    87   83    83    72.6                                __________________________________________________________________________    % Gain     1.9%   18.4% 19.8% 14%   14%   --                                  __________________________________________________________________________                                           Control                                               3200 ppm.                                                                             1600 ppm.                                                                             800 ppm.                                                                              0                                                     Height                                                                            Number                                                                            Height                                                                            Number                                                                            Height                                                                            Number                                                                            Height                                                                            Number                                Compound    Inches                                                                            Leaves                                                                            Inches                                                                            Leaves                                                                            Inches                                                                            Leaves                                                                            Inches                                                                            Leaves                             __________________________________________________________________________    1-(3-chlorophthal-                                                             imido)cyclohexane-                                                                          75  47  78  50  54.5                                                                              45  38* 43*                                 carboxamide                           42**                                                                              48**                               __________________________________________________________________________      *Replicate I                                                                 **Replicate II                                                           

EXAMPLE 40 Effect of Phthalimide Derivative on Potato Plants

In these tests, 50/50 aqueous/acetone mixtures containing from 0 to10,000 ppm. of 1l -(3-chlorophthalimido)cyclohexanecarboxamide areprepared. Seed pieces of potato (Superior variety) are dipped for 1 or 5minutes in the selected solution and then planted in flats and placed inthe greenhouse. The plants are cared for in accordance with normalgreenhouse procedures, and two months after treatment and the plants areexamined. The number of shoots and tubers developed are counted, theheight and weight of the shoots and the root weight is also determined.These data are reported below in Table XVIII, where it can be seen thatthere is a 22% to 60% increase in shoot number, a 2% to 134% increase inshoot height, up to 63% increase in shoot weight, up to 170% increase intuber number, and as much as 53% increase in root weight.

                                      TABLE XVIII                                 __________________________________________________________________________    Effect of 1-(3-Chlorophthalimido)cyclohexanecarboxamide on Dipped Potato      Tubers (Superior Variety)                                                     Shoot Number           Shoot Height (cm.)                                                                             Shoot Weight (grams)                                      Plus             Plus                   Plus                                  or               or                     or                Replicate           Mi-                                                                              Replicate     Mi-                                                                              Replicate           Mi-               Treatment                                                                           I  II III                                                                              Average                                                                            nus %                                                                            I  II III                                                                              Average                                                                            nus %                                                                            I    II   III  Average                                                                            nus               __________________________________________________________________________                                                                %                 *A-1  7  5  6  6    -- 33 42 48 41   -- 116.8                                                                              126.2                                                                              135.6                                                                              126.2                                                                              --                A-2   7  5  10 7.3  +22%                                                                             50 50 48 49   +19%                                                                             153  136.7                                                                              153.5                                                                              147.7                                                                              +16%              A-3   6  7  9  7.3  +22%                                                                             50 48 46 48   +17%                                                                             130  109.7                                                                              128.2                                                                              122.6                                                                               -4%              A-4   9  6  7  7.3  +22%                                                                             60 68 65 64   +56%                                                                             134.5                                                                              139.8                                                                              129.3                                                                              134.5                                                                               +4%              A-5   8  9  7  8    + 33%                                                                            90 90 110                                                                              96   +34%                                                                             165.4                                                                              161.3                                                                              88.0 138.2                                                                               +9%              __________________________________________________________________________    B-1   6  4  5  5    -- 46 56 50 50   -- 111.2                                                                              105.5                                                                              116.8                                                                              111.1                                                                              --                B-2   8  8  6  7.3  +46%                                                                             50 50 55 51    +2%                                                                             154  130  148.6                                                                              144.2                                                                              +29%              B-3   7  9  6  7.3  +46%                                                                             53 55 58 55   +10%                                                                             118.7                                                                              106.8                                                                              141.4                                                                              122.3                                                                               +9%              B-4   10 9  6  8.3  +66%                                                                             73 83 65 73   +46%                                                                             147.1                                                                              174.1                                                                              145  155.4                                                                              +39%              B-5   7  9  8  8    +60%                                                                             94 100                                                                              105                                                                              99   +98%                                                                             177.3                                                                              181.5                                                                              186.5                                                                              181.7                                                                              +63%              __________________________________________________________________________                         Tuber Number      Root Weight (grams)                                                       Plus                    Plus                                                  or                      or                                      Replicate     Minus                                                                             Replicate           Minus                             Treatment                                                                           I  II III                                                                              Average                                                                            %   I    II   III  Average                                                                            %                                 *A-1  10 10  8 9.3  --  69.5 75.3 86.7 77.1 --                                A-2    5 13  9 9     -4%                                                                              132.6                                                                              82.3 86.3 100.5                                                                              +30%                              A-3   14  9  8 10.3  +7%                                                                              115.3                                                                              81.3 76.6 91.0 +18%                              A-4    7  7 15 9.6   +3%                                                                              111.2                                                                              103.4                                                                              88.4 101.0                                                                              +31%                              A-5   11 27 20 19.3 +107%                                                                             104.7                                                                              129  122.4                                                                              118.7                                                                              +53%               __________________________________________________________________________                   B-1    9  9  6 8    --  --   78.7 86.4 82.5 --                                B-2   11  9 12 10.6  +32%                                                                             101.4                                                                              195.7                                                                              83.3 126.8                                                                              +53%                              B-3   10  6 10 8.6   +7%                                                                              86.5 67.8 96.8 83.7 +1%                               B-4   16 19 10 15    +87%                                                                             104.8                                                                              122  99.6 108.8                                                                              +31%                              B-5   15 32 18 21.6 +170%                                                                             86.1 94.1 140  106.7                                                                              +29%               __________________________________________________________________________    *Concentrations:                                                                       1 = 0 ppm.                                                                              Duration of Dip A = 1 minute                                        2 = 10 ppm.                                                                             Duration of Dip B = 5 minutes                                       3 = 100 ppm.                                                                  4 = 1,000 ppm.                                                                5 = 10,000 ppm.                                                      __________________________________________________________________________

EXAMPLE 41 Effect of Phthalimide Derivatives on Woody Plants

In these tests, resting Euonymous (woody) plants growing in individualpots are treated with 50/50 aqueousacetone solutions containingsufficient amounts of the test phthalimide to provide 0, 5 or 15 poundsper acre thereof. The phthalimides used are4-chloro-α-isobutyl-α-methyl-1,3-dioxo-2-isoindolineacetamide and1-(3-chlorophthalimido)cyclohexanecarboxamide, and application is madeas a soil drench. The plants are measured and the number of branchescounted at treatment. Two months after treatment, the plants are againmeasured and the number of branches counted. Data obtained are reportedbelow in Table XIX where it can be seen that there is a 10% to 55%increase in leader growth and a 23% to 54% increase in the number ofbranches on treated plants.

                                      TABLE XIX                                   __________________________________________________________________________    Effect of 4-Chloro-α-isobutyl-α-methyl-1,3-dioxo-2-isoindoline    acetamide                                                                     and 1-(3-Chlorophthalimido)cyclohexanecarboxamide on Euonymous                Soil Drench Treatment                                                                                                                  Average                             Height of  Number   Leader -        Average                                                                             %                                   Leader in cm.                                                                            Branches Added Growth                                                                          Number  %     Increase                            at Treatment                                                                             at Treatment                                                                           in cm.  Branches                                                                              Leader                                                                              in                                                                      Growth                                                                              Number                         Rate Replicate  Replicate                                                                              Replicate                                                                             Replicate                                                                             Four  of                   Compound  lbs./acre                                                                          I  II III                                                                              IV                                                                              I II III                                                                             IV                                                                              I II                                                                              III                                                                             IV                                                                              I II                                                                              III                                                                             IV                                                                              Replicates                                                                          Branches             __________________________________________________________________________    1-(3-chlorophthal-                                                             imido)cyclohexane-                                                                     15   24 21.5                                                                             37 41                                                                              6 9  2 2 17                                                                              21                                                                              8 23                                                                              9 9 4 4 +55%   +36%                 carboxamide                                                                            5    21.5                                                                             25.5                                                                             32 38                                                                              3 6  6 2 9 9 12                                                                              7 4 7 7 3 + 31%  +23%                4-chloro-α-isobutyl-                                                    methyl-1,3-dioxo-                                                              2-isoindoline-                                                                         15   19.5                                                                             21.5                                                                             43.5                                                                             28                                                                              6 5  5 7 2 4 2 4 8 6 10                                                                              8 +10%   +40%                 acetamide                                                                              5    21.5                                                                             24 31 38                                                                              4 10 3 3 4 8 2 7 5 11                                                                              9 6 +18%   +54%                    Control                                                                             0    39.5                                                                             39.5                                                                             23.5                                                                             23                                                                              4 6  6 6 0 0 0 0 4 6 6 6  0%     0%                     Control                                                                             0    28 21.5                                                                             16.5                                                                             24                                                                              7 14 2 4 0 0 0 0 7 14                                                                              2 4  0%     0%                 __________________________________________________________________________

EXAMPLE 42 Effect of Phthalimido Derivatives on Pod Setting of Soybeans

In these tests, soybeans (cv Corsoy) are planted in individual pots andtreated with 50/50 aqueous/acetone mixtures containing from 0 to 2pounds per acre of the active phthalimide,1-(3-chlorophthalimido)cyclohexanecarboxamide. The pots are then placedin the greenhouse and cared for in usual fashion. Two months aftertreatment, the plants are examined and the height of attachment of thefirst pod above the ground determined for each plant. From the dataobtained, it can be seen in Table XX that the height of attachment ofthe first pod of treated plants is from 10 to 22 centimeters above thoseof untreated plants.

                  TABLE XX                                                        ______________________________________                                                      Rate      cm. Above Ground of                                   Compound      lbs./acre Attachment of First Pod                               ______________________________________                                        0             --        12 cm.                                                1(3-chlorophthal-                                                             imido)cyclohex-                                                                             1         20 cm.                                                anecarboxamide                                                                              2         32 cm.                                                ______________________________________                                    

EXAMPLE 43 Evaluation of Phthalimides for Plant Growth Regulant Activity

In these tests, containers are filled to within one-half inch of the topwith greenhouse potting soil, tamped, and three Amsoy soybeans areplaced in each pot. The pot is filled to the top with soil in whichKentucky 31 Fescue seeds have been mixed in an amount sufficient toprovide each pot with approximately 625 Fescue seeds.

To prepare the test compounds, 20 mg. of the compound is placed into atwo-ounce, wide-mouth glass bottle and dissolved or dispersed in a 50/50acetone/water mixture sufficient to prepare a 1,000 ppm. solution orsuspension.

An addition of 5 ml. of the 1,000 ppm. solution in each cup isequivalent to 10 lbs./acre.

Just prior to the application of the compounds, the test pots arelightly watered to prevent formation of air pockets and channellingroutes during application which would prevent even distribution of thetest compound in the soil. Application is accomplished by dispensing 5ml. of solution or suspension evenly over the surface of the soil with apipettor. Three replications are used for each compound.

The test is conducted weekly. Each test includes 5 ml. of 1:1acetone:water controls, 5 ml. water controls as a standard forcomparison of activity from test to test. The treated plants are benchedin the greenhouse and normal watering practices are followed. Minimumday and night temperatures of 65°F. are maintained during coolerportions of the year. Normal daily temperature fluctuations occur duringthe summer season. Data obtained are reported below in Table XXI.

Data Recording

Initial observations are made at three to five days after treatment forearly germination of both test species. Physiological or morphologicalchanges from the norm are noted during the test period. Finalobservations are made at two to three weeks after treatment (dependenton time of year). At this time, measurements of the height of plants ofboth species are made. From these measurements percent increases ordecreases as compared to control plants are calculated.

                                      TABLE XXI                                   __________________________________________________________________________    10 lbs/Acre Preemergence                                                      % Increase or Decrease in Height Compared to Control                                          Soybeans      Fescue                                                          First  Final  First  Final                                    Compound        Measurement                                                                          Measurement                                                                          Measurement                                                                          Measurement                              __________________________________________________________________________    1-Phthalimidocyclo-                                                           hexanecarboxamide                                                                             --     58 E.G.*                                                                             --     46 E.G.                                  α-(3-chlorophthal-                                                      imido)-α-isopropyl-                                                     α-methylacetamide                                                                       28     36 Phy.                                                                              38     36 Phy.                                  α-(3-chlorophthal-                                                      imido)-α-isobutyl-                                                      α-methylacelamide                                                                       N      N      21     15                                       Cyclohexanecarbox-                                                            amide, 1-(3-chloro-                                                           phthalimido)-   73 (7-10)                                                                            73 (7-21)                                                                            51     49                                       Cyclopentanecarbox-                                                           amide, 1-(3-chloro-                                                           phthalimido)    N      cut    24     10                                       Cyclohexanecarboxylic                                                         acid, 1-phthalimido-                                                                          -13    cut    -33    -31                                      Cyclopentanecarbox-                                                           amide, 1-phthalimido-                                                                         --     23 E.G.                                                                              --     17 E.G.                                  Cycloheptanecarbox-                                                           amide, 1-(3-chloro-                                                           phthalimido)-   --     N D.G. --     41 D.G.                                  Cyclohexanecarboxylic                                                         acid, 1-(3-chlorophthal-                                                      imido)-,2,2-dimethyl-                                                         hydrazide       --     N      --     11                                       Cyclohexanecarbox-                                                            amide, 1-(3-chloro-                                                           phthalimido)-N-methyl-                                                                        29     --     25     --                                       Cycloheptanecarbox-                                                           amide, 1-(3-methylphthal-                                                     imido)-         24     --     53     --                                       Cycloheptanecarbox-p-                                                         anisidide, 1-(3-methyl-                                                                       N      --     33     --                                       phthalimido)-                                                                 Cycloheptanecarboxylic                                                        acid, 1-(3-methylphthal-                                                      imido)-, 2,2-dimethyl-                                                        hydrazide       N      --     29     --                                       Cycloheptanecarboxylic                                                        acid, 1-(3-methylphthal-                                                      imido)-, methyl ester                                                                         -20    --     17     --                                       Cyclohexanecarboxylic                                                         acid, 1-(3-acetamido-                                                         phthalimido)-   14     --     22     --                                       Cyclopentanecarboxamide,                                                      1-(3-chlorophthalimido)-                                                      N-methyl-       N      --     32     --                                       Cyclopentanecarboxamide,                                                      1-(4-chlorophthalimido)-                                                                      31     -- E.G.                                                                              35     -- E.G.                                  Cyclohexanecarboxamide,                                                       1-(4-methylphthalimido)-                                                                      31     -- E.G.                                                                              50     -- E.G.                                  Cyclohexanecarboxanilide,                                                     4'-chloro-1-(4-methyl-                                                        phthalimido)-   N      --     25     --                                       Cyclohexanecarboxy-o-                                                         toluidide, 3'-chloro-                                                         1-(4-methylphthal-                                                            imido)-         11     --     28     --                                       Cyclohexanecarboxylic                                                         acid, 1-(4-methylphthal-                                                      imido)-, 2,2-dimethyl-                                                        hydrazide       16     --     25     --                                       Cyclopentanecarboxylic                                                        acid, 1-(4-methylphthal-                                                      imido)-         11     --     21     --                                       Cyclopentanecarboxamide,                                                      1-(3-chlorophthalimido)-                                                      N,N-dimethyl-   19     --     19     --                                       Cyclohexanecarboxy-m-                                                         toluidide, 4'-chloro-1-                                                       (3-chlorophthalimido)-                                                        α,α,α,-trifluoro-                                                           23     --     26     --                                       Cyclohexanecarboxamide,                                                       1-(4-chlorophthal-                                                            imido)-         21     53 E.G.                                                                              50     41 E.G.                                  Cyclohexanecarboxamide,                                                       1-(3-acetamidophthal-                                                         imido)-N-methyl-                                                                              N      -24    14     N                                        Cyclohexanecarbox-p-                                                          anisidide, 1-(3-iodo-                                                         phthalimido)-   N      N      14     N                                        Cyclohexanecarboxamide,                                                       1-(3-iodophthalimido)-                                                                        N      26     28     28                                       Cyclohexanecarboxamide,                                                       1-(3-fluorophthal-                                                            imido)-         51     39     48     41                                       Cyclopentanecarboxamide,                                                      1-(3-methylphthalimido)-                                                                      46     48 E.G.                                                                              28     27 E.G.                                  Cyclohexanecarboxamide,                                                       1-(3-methylphthalimido)-                                                                      60     66 E.G.                                                                              39     56 E.G.                                  Cyclooctanecarboxamide,                                                       1-(4-chlorophthalimido)-                                                                      N      N      N      N                                        Cyclohexanecarboxamide,                                                       1-(3-bromophthalimido)-                                                                       46     44     47     56                                       Cyclohecanecarboxamide,                                                       1-(1,2,3,6-tetrahydro-                                                        phthalimido)-1- N      -23    12     N                                        Cyclohexanecarboxamide,                                                       1-(1-cyclohexene-1,2-                                                         dicarboximido)- 51            61                                              Cyclohexanecarboxamide,                                                       3-methyl-1-(3-methyl-                                                         phthalimido)-trans(CH.sub.3                                                   to CONH.sub.2)- 27            53                                              Cyclohexanecarboxylic                                                         acid, 3-methyl-1-(3-                                                          methylphthalimido)-,                                                          trans(CH.sub.3 to COOH)-                                                                      N             11                                              Cyclohexanecarboxamide,                                                       1-(hexahydrophthal-                                                           imido)          N      N      28     26                                       Cyclohexanecarboxamide,                                                       1-(4-methyl-hexahydro-                                                        phthalimido)    N             18                                              __________________________________________________________________________    *Phy = phytotoxic                                                             N    = normal                                                                 A.G. = acillary growth                                                        D.G. = delayed     Special Test - Phthalimide Activity Evaluation                    -  germination                                                         E.G. = early germination                                                      --   = not read for that                                                             particular test                                                               (either 1st or 2nd)                                                

Cotton seed from plants treated at 2 pounds per acre with compounds ofthe invention at the time of first bloom and seed from untreatedcontrols in the same experiment were planted 5 seeds per 6 inchesplastic pot in the spring. There were 4 pots of each type seed, treatedand untreated. Treated seedlings broke through the surface on March 17(19 of 20 seeds emerged, 95% emergence) whereas 7 of 20 seeds of theuntreated controls emerged (35% emergence). On March 26 at terminationof the test, treated stand was 95% and controls were 50%. These datasuggest that treated plants impart better viability to the seed.

EXAMPLE 44 Evaluation of Phthalimides for Plant Growth Regulant Activity

In these tests plastic containers are filled with potting soil to withinthree-fourths inch of the top. Seeds of Cherry Belle radishes andKentucky 31 fescue are then placed on the soil surface and covered withone-half inch of potting soil. A tamper is used to level the soilsurface and to firm the soil. After planting the pots are sprayed with a1:1 water acetone mixture containing sufficient compound to provide fromabout 0.13 to 8.0 pounds per acre of test compound. The treated pots areplaced in the greenhouse and watered when needed. Fourteen days aftertreatment the pots are examined and the plants removed, washed andweighed. Fescue and radishes grown in untreated soil are used ascontrols and data obtained are reported in Table XXII below.

                                      TABLE XXII                                  __________________________________________________________________________    Plant Growth Regulant Activity of Compounds Having the Formula:                                                     Fescue     Radish Fresh Weight          X        X'      lb/Acre                                                                             R.sub.1    R.sub.2                                                                           Fresh Weight (g)                                                                         Whole (g)                                                                            Root                  __________________________________________________________________________                                                            (g)                                    0.5                  17.9       60.2   46.8                  3-OC.sub.2 H.sub.5                                                                     6-OC.sub.2 H.sub.5                                                                    2.0       --(CH.sub.2).sub.5 --                                                                    21.8       59.6   45.8                  3-SO.sub.2 C.sub.2 H.sub.5                                                             6-CH.sub.3                                                                            0.5       --(CH.sub.2).sub.5 --                                                                    18.4       61.0   46.5                                   2.0                  15.6       48.7   37.9                  4-CH.sub.3                                                                             5-CH.sub.3                                                                            0.13      --(CH.sub.2).sub.5 --                                                                    17.7       61.8   48.7                  Check            0                    17.1       55.4   41.8                  3-CH.sub.3                                                                             6-CH.sub.3                                                                            2.0       --(CH.sub.2).sub.5 --                                                                    28.4       74.5   55.9                  3-OC.sub.2 H.sub.5                                                                     5-OC.sub.2 H.sub.5                                                                    8.0       --(CH.sub.2).sub.5 --                                                                    25.7       76.5   59.3                  Check            0                    26.3       62.2   44.9                  3-Br     4-Br    2.0       --(CH.sub.2).sub.5 --                                                                    34.6       55.1   39.3                  Check            0                    27.1       61.5   44.8                  Check            0                    27.1       61.5   44.8                  4-OCH.sub.3                                                                            H       0.13      --(CH.sub.2).sub.5 --                                                                    26.8       77.0   56.5                  4-OCH.sub.2 C.sub.6 H.sub.5                                                            H       0.5       --(CH.sub.2).sub.5 --                                                                    27.9       79.3   59.5                                   2.0                  35.8       60.3   59.5                  3-CF.sub.3                                                                             H       0.5       --(CH.sub.2).sub.5 --                                                                    35.4       68.5   52.1                                   2.0                  35.4       77.4   58.7                                   8.0                  41.7       54.2   39.9                  __________________________________________________________________________

We claim:
 1. A compound having the formula: ##SPC53##or ##SPC54##wherein W is hydrogen or alkyl C₁ -C₄ ; X and X' each representshydrogen, halogen, alkyl C₁ -C₄, CF₃, alkoxy C₁ -C₄, benzyloxy, di(C₁-C₄)alkylamino, C₁ -C₄ alkylthio, hydroxy, C₁ -C₄ alkylsulfonyl,alkanoylamino C₁ -C₄ or nitro; Y is --CONHR₈ ---CONR₃ R₄, --CONHN(R₅)₂,--CONHN⁺(R₆)₃ .halide⁻ --CN or --COR₇ with the proviso that at least oneof X and X' is a substituent other than hydrogen; R₁ and R₂ eachrepresent alkyl C₁ -C₄ or when taken together with the carbon to whichthey are attached form cycloalkyl C₄ -C₁₁ optionally substituted withmethyl; R₃ and R₄ each represent hydrogen or alkyl C₁ -C₄ ; R₅ and R₆each represent alkyl C₁ -C₂, R₇ is halogen, R₈ is --CH₃ or ##SPC55##where Z and Z' are hydrogen, alkyl C₁ -C₂, halogen, --CF₃ or --OCH₃ andis a single or double bond with the proviso that there be only 0 or 1double bond in the ring.
 2. A compound according to claim 1 wherein Y is--CONR₃ R₄.
 3. A compound according to claim 1 wherein Y is--CONHN(R₅)₂.
 4. A comppound according to claim 1 wherein Y is--CONHN⁺(R₆)₃ .halide⁻.
 5. A compound according to claim 1 wherein Y is--CN.
 6. A compound according to claim 1 wherein Y is --COR₇.
 7. Acompound according to claim 1, wherein Y is --CONHR₈.
 8. A compoundaccording to claim 2, 1-(3-chlorophthalimido)cyclohexanecarboxamide. 9.A compound according to claim 2,1-(3-chlorophthalimido)cyclopentanecarboxamide.
 10. A compound accordingto claim 2, 1-(4-chlorophthalimido)cyclohexanecarboxamide.
 11. Acompound according to claim 2,1-(4-methylphthalimido)-1-cyclohexanecarboxamide.
 12. A compoundaccording to claim 2,1-(3,4,5,6-tetrahydrophthalimido)-1-cylohexanecarboxamide.
 13. Acompound according to claim 2,α-isobutyl-α-methyl-α-(3-chlorophthalamido)acetamide.
 14. A compoundaccording to claim 2,1-(3-trifluoromethylphthalimido)cyclohexanecarboxamide.
 15. A compoundaccording to claim 2,1-(3,5-dichlorophthalamido)-1-cyclohexanecarboxamide.
 16. A process forthe preparation of compounds having the formula: ##SPC56##or ##SPC57##wherein W is hydrogen or alkyl C₁ -C₄ ; X and X ' each representhydrogen, halogen, alkyl C₁ -C₄, CF₃, alkoxy C₁ -C₄, benzyloxy, di(C₁-C₄)alkylamino, C₁ -C₄ alkylthio, hydroxy, C₁ -C₄ alkylsulfonyl,alkanoylamino C₁ -C₄, or nitro; Y is --CN or CONH₂ ; R₁ and R₂ eachrepresent alkyl C₁ -C₄ or when taken together with the carbon to whichthey are attached form cycloalkyl C₄ -C₁₁ optionally substituted withmethyl; and is a single or double bond, with the proviso that there beonly 0 or 1 double bond in the ring; comprising reacting a compoundhaving the formula: ##SPC58## or ##SPC59## where X, X', W and are asdescribed above, with a compound having the structure: ##EQU6## where R₁and R₂ are as described above, in the presence of an inert solvent at atemperature between 20°C. and 60°C. to give the phthalamic acid;treating the thus-formed phthalamic acid with a dehydrating agent ofacetic anhydride, acetylchloride or thionyl chloride at a temperature offrom 0°C. to 100°C. to yield the phthalimidonitrile and treating thethus-formed phthalimidonitrile with a strong acid at a temperaturebetween about -10°C. and 30°C. to form the phthalimido acetamide.